Zalcitabine

From Citizendium, the Citizens' Compendium
Jump to: navigation, search
This article is developing and not approved.
Main Article
Talk
Related Articles  [?]
Bibliography  [?]
External Links  [?]
Citable Version  [?]
 
This editable Main Article is under development and not meant to be cited; by editing it you can help to improve it towards a future approved, citable version. These unapproved articles are subject to a disclaimer.
Zalcitabine strucure.jpg
zalcitabine
IUPAC name: see chemistry section
Synonyms: dideoxycytidine (ddC)
Formula: C9H13N3O3

 Uses: HIV/AIDS

 Properties: RT inhibitor, cytosine analog, DNA terminator

 Hazards: see drug interactions

Mass (g/mol): CAS #:
211.2178 7481-89-2


Zalcitabine, or dideoxycytidine (DDC or DDCYD), is a dideoxynucleoside antiviral drug that is an analog of the natural DNA base cytosine. The lack of 3'-hydroxyl group makes it a viral DNA chain terminator. It also inhibits HIV-1 reverse transcriptase by binding to it and competing with the natural substrate deoxycytidine triphosphate (dCTP). The related drug lamivudine, which has a sulfur atom in place of the 3'-carbon present in zalcitabine, suppresses viruses in a similar manner.

Chemistry

Its IUPAC chemical name of zalcitabine is 4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one, but it is also called dideoxycytidine (ddC), and it has molecular formula C9H13N3O3 giving it a molecular mass of 211.2178 g/mol. It is a structural analog of the natural base deoxycytosine which used in DNA, but zalcitabine lacks the 3'-hydroxy group.

External links

The most up-to-date information about Zalcitabine and other drugs can be found at the following sites.